Pod Insights Here's The Thing with Alec Baldwin Chris Whipple is Still Covering the White House About this episode Chris Whipple is an Emmy award-winning journalist, documentary filmmaker, author, and political analyst. A former CBS 60 Minutes producer, Whipple is also the EP and writer of the Discovery Channel documentary series “The Presidents’ Gatekeepers” and the Showtime Network documentary series “The Spymasters: CIA in the Crosshairs”. Whipple continued his research on these topics in two of his books and is the author of four New York Times best-sellers including: Uncharted: How Trump Beat Biden, Harris, and the Odds in the Wildest Campaign in History, The Spymasters: How the CIA Directors Shape History and the Future, The Gatekeepers: How the White House Chiefs of Staff Define Every Presidency, and The Fight of His Life: Inside Joe Biden's White House. Whipple has also written for Vanity Fair, Politico, the Daily Beast, and many other publications. Notably, Whipple wrote the two-part 2025 Vanity Fair profile on the second Trump presidency and White House Chief of Staff, Susie Wiles.
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1:37 Alec Baldwin? This is Alec Baldwin, and you're listening to Here's the Thing from iHeart Radio. In today's world of endless scrolling and 24-hour news cycles, it's rare for any one piece of journalism to become culturally relevant. But that is precisely what happened to a piece written by my guest today. Chris Whipple's groundbreaking profile of White House Chief of Staff Susie Wiles became one of Vanity Fair's most-read stories of 2025. The piece was debated constantly on TV news, and photos of Wiles and her staff from the article were shared across the Internet for weeks.
2:18 Alec Baldwin? Along with his work for Vanity Fair, Chris Whipple is an Emmy-winning journalist, author, and documentary filmmaker. Described as "an indispensable observer of American power." Whipple has written for publications such as Politico and The Daily Beast. He's also authored four nonfiction books on American politics and government. Working in so many different mediums, I wanted to know what Whipple considers himself to be.
2:48 Speaker 06 A little bit of all of the above, I guess. I have clearly, I've got some kind of identity crisis going on. I stumbled into this latest phase of my career, writing books about political history, and it happened with a phone call out of the blue from a couple of French brothers named Jules and Julien Nadey, who had done the iconic documentary 9/11. They almost died that day. They said, "Chris, we have this crazy idea. We want to do a documentary about White House Chiefs of Staff." And I thought about that for about 30 seconds, and I said, "I'm in."
3:25 Alec Baldwin? So they produced the documentary, which you did for Discovery?
3:27 Speaker 06 We did it together, the three of us. I did the interviewing. We all did the producing and editing together. They directed.
3:34 Alec Baldwin? You wrote it?
3:35 Speaker 06 Yeah.
3:36 Alec Baldwin? So before we get into any details about the Wiles piece for Vanity Fair, I think it's safe to say, and you wrote a book about these folks, that was she perhaps? I didn't really see Wiles on the scene very much in the first administration. Was she there with him in the first administration?
3:50 Speaker 06 No, she was not.
3:51 Alec Baldwin? Who was his chief of staff then?
3:52 Speaker 06 So he went through four chiefs of staff, beginning with Reince Priebus, followed by John Kelly, General John Kelly, followed by Mick Mulvaney, followed by the ultimate sycophant, Mark Meadows. I wrote a piece about Meadows, calling him the worst chief of staff in history, and there was stiff competition for that.
4:10 Alec Baldwin? Right, right, right. And he qualified as worst, why?
4:13 Speaker 06 Because he was the ultimate, he was the guy, Donald Trump. Was desperately wanted, namely, somebody who would just refuse to push back in any way and say, yes, boss, and salute every time Trump came up with a cockamamie idea.
4:30 Alec Baldwin? He just rubber stamped everything.
4:31 Speaker 06 Yeah, exactly. He was the ultimate sycophant.
4:33 Alec Baldwin? Right. But Wiles is in this second term. She started the second term.
4:37 Speaker 06 Correct.
4:38 Alec Baldwin? She's been with him throughout this past year or so.
4:39 Speaker 06 That's right. That's right.
4:40 Alec Baldwin? And Wiles, I don't really read very much about her. I didn't really have much of a sense of her until this piece came out in Vanity Fair.
4:47 Speaker 06 Yeah. Listen, I think Susie Wiles, in my view, was maybe the most fascinating person in American politics, and partly because she engineered this unbelievable, against-all-odds 2024 presidential campaign for Donald Trump. Donald Trump would not be president without her, in my view. So, for openers, she had that going for her. Beyond that, she was a, she has this fascinating story. You know, the daughter of Pat Summerall, the famous sportscaster who was an alcoholic, and she came up through the traditional GOP as a
5:25 Speaker 06 kind of Reagan Republican, became disillusioned with that. Then she found Donald Trump, and along the way, she got Ron DeSantis elected. That's another wild story. DeSantis turned on her and threw her under the bus and tried to destroy her career.
5:43 Alec Baldwin? She's a Floridian?
5:44 Speaker 06 She's a Floridian. She's been through the wars, and she was rewarded, after having won this against-all-odds campaign in 2024 for Trump, she was rewarded with the job of White House Chief, the first woman ever to serve as White House Chief of Staff.
6:01 Alec Baldwin? What do you think was her contribution to the campaign? How did she help him get elected?
6:04 Speaker 06 Well, in many ways. I mean, she, first of all, she has a kind of magic with Trump that none of her predecessors had, either campaign managers or White House Chiefs of Staff for that matter. He trusts her in a way that he never trusted anyone else. She's without a doubt the second most powerful person in the Trump White House. And she earned it the hard way. There's a great story that I tell in the Vanity Fair piece about the time that Trump in 2016 called her into his golf club and in front of a bunch of cronies proceeded to just take her apart over, abuse her verbally over
6:44 Speaker 06 a poll that he didn't like, that showed him losing in Florida. Well, she sat there, she said she didn't know whether to flee or what she really wanted to do was cry, but instead she steeled herself and she said, "Mr. Trump, if you want somebody to set her hair on fire, I'm not your girl. But if you want somebody to win Florida, I am." And she turned on her heel and walked out. And she says that every day thereafter, Trump was on the phone calling her for help.
7:15 Alec Baldwin? Now, I don't know as much about this, obviously, as you do, but sometimes I wonder, where someone who has this privileged position, someone who's worked their magic with Trump and it's working, she has his ear all the time and is an important figure in that administration, then she does an interview with you. And I think to myself, do you catch some of these people on a day where they're just fed up and they really decide they want to talk?
7:37 Speaker 06 Well, in this case, it would have to be 11 days, over 11 months.
7:42 Alec Baldwin? She really wanted to talk.
7:43 Speaker 06 She really wanted to talk. You know, I've read all the stories, the speculation that she was, this was a Machiavellian maneuver on her part to take J.D. Vance down a notch and elevate Rubio and position herself and distance herself from some of the problems, the pardons and all the rest of it. And I don't, I think it's a lot simpler than that. I think that, number one, I ran into Walter Isaacson the week that the story dropped, and Walter came up and gave me a big hug and he said, "You know what, Chris? People just like to talk. People want to tell their story, especially if they think they're going to get a fair hearing." So that was part of it. I think I came with a reputation for
8:28 Speaker 06 being nonpartisan. You know, I'd praised some Republican White House chiefs. She knew I'd written, she'd read my book about the White House Chiefs, the staff, the gatekeepers. So that helped. But the other thing that I think is really key here is that every White House chief, every White House staffer, Lives in a bubble. They work in a bubble called the West Wing. And it's exponentially more so in the Trump White House. Where you're sitting around talking to acolytes, all of them reading from the same playbook. And I think at a certain point, you forget that all this crazy stuff you're talking about sounds insane on planet Earth.
9:12 Speaker 06 And I think at a certain point, she thinks she's talking to Stephen Miller. And when the whole thing landed a couple of weeks ago, it was a problem.
9:22 Alec Baldwin? Now, what was your journalistic DNA when you were a kid? What did your dad do?
9:26 Speaker 06 My dad was a journalist, so that's how it started. So I caught the bug.
9:30 Alec Baldwin? Who did you write for?
9:31 Speaker 06 He was an editor of the Weekly Life magazine back in the glory days of, you know, the 60s. And so I caught the bug around the dinner table. His friends were writers like Walter Lord. Rachel Carson came over for dinner.
9:44 Alec Baldwin? In Washington?
9:45 Speaker 06 In, no, in Connecticut.
9:47 Alec Baldwin? Oh, wow.
9:47 Speaker 06 He commuted to New York where he worked. So, you know, Alfred Eisenstadt, the photographer, would come over. You know, so I caught that bug early on. This is pretty exciting stuff, just covering the world.
9:59 Alec Baldwin? So your home and journalism affects you like you're reading the New York Times when you're 10 years old? How does it start for you, your curiosity?
10:08 Speaker 06 It started, again, around the dinner table. This just seemed like a pretty exciting way to have a career. Covering stories, you know, all over the world. And again, those were the glory days of Life and Look and Saturday Evening Post and.
10:23 Alec Baldwin? Seven newspapers in New York a day?
10:25 Speaker 06 Yeah, exactly. So that was pretty exciting. And I, so right out of college, I got a job working for Foreign Policy Magazine. Dick Holbrook was my boss.
10:34 Alec Baldwin? I want to get to him.
10:35 Speaker 06 And then I went to the Monthly Life Magazine, which made a run around 1978 to the late 80s. And so for eight years. I traveled all over the world. I mean, I went to South Africa and lived with Winnie Mandela for a while.
10:49 Alec Baldwin? I want to ask you about that.
10:49 Speaker 06 I went from there to...
10:51 Alec Baldwin? You're reading my notes here.
10:53 Speaker 06 I went to the Philippines and, you know, met Ferdinand and Amelda Marcos.
10:56 Alec Baldwin? Back in the day when journalists like that were traveling a great deal, they don't do that much anymore.
11:00 Speaker 06 That's right. We'd go for weeks, sometimes...
11:03 Alec Baldwin? You have kids?
11:04 Speaker 06 Sometimes months at a time.
11:05 Alec Baldwin? Do you have children?
11:06 Speaker 06 I didn't at that point.
11:07 Alec Baldwin? But you?
11:08 Speaker 06 Yeah, I do now.
11:09 Alec Baldwin? Well, I mean, you probably didn't have any time.
11:10 Speaker 06 Yeah, yeah.
11:11 Alec Baldwin? It's probably wise of you not to have children when you're flying all over the world.
11:13 Speaker 06 Right.
11:14 Alec Baldwin? Now, talk about Mandela, for example. I remember, when you were with her, was this, before, after, during, "They will wear our necklaces" stuff?
11:21 Speaker 06 It was right during, right at that moment. I mean, she was lionized, she was idolized, she was the so-called "Mother of the Nation." "Mama, wait till..." You'd hear the people chant when she walked through the streets of Soweto. At one point, David Turnley, the photographer for Life, and I were surrounded by an angry group of kids, and we thought we might be next to be "necklist," as they called it.
11:47 Alec Baldwin? I remember that.
11:48 Speaker 06 Necklacing was the practice of, if they thought you were a police informer, and we were a couple of white guys in the middle of Soweto, they would pour gasoline over a tire.
12:00 Alec Baldwin? Of course.
12:01 Speaker 06 Put it around your neck and set it on fire.
12:02 Alec Baldwin? I remember she said in that speech, "They will wear our necklaces." She's condemning somebody at that speech.
12:07 Speaker 06 So, we, you know, at one point, we were surrounded by these kids, and they were suspicious, and suddenly, we saw the crowd part, and we saw Winnie Mandela coming through, and she said, "These are my friends," and she led us back to her house.
12:21 Alec Baldwin? Just in time.
12:22 Speaker 06 Yeah, just in time.
12:23 Alec Baldwin? What did you talk to her about?
12:24 Speaker 06 Well, mostly about "the struggle," as they put it. Nelson Mandela was still in prison at that point.
12:29 Alec Baldwin? Robyn's Island.
12:30 Speaker 06 He was actually in Polesmore Prison at that point. He'd been moved from Robyn Island, where he spent most of those years, to a place called Polesmore. We actually went into the waiting room with Winnie posing as a couple of her lawyers, hoping to get a glimpse of Nelson, and nobody had seen him since... Early 60s, since the Ravonia trial. And we were hoping that Winnie would take a miniature camera in and get a picture for us.
12:54 Alec Baldwin? She wouldn't do it?
12:55 Speaker 06 For life. Well, she said she couldn't. She said she tried. Anyway, Winnie was a absolutely fascinating, charismatic, and really complicated, ultimately tragic, character, I think.
13:09 Alec Baldwin? Tragic, why?
13:10 Speaker 06 Tragic because I think that she, as she would be the first to admit, she was much more radical than her husband Nelson. She was much less prepared to forgive. And I think she also thought, and you could argue maybe rightly, that having spent all those years struggling to advance the revolution.
13:35 Alec Baldwin? In his absence.
13:37 Speaker 06 In his absence. That she was owed something, I think, in her mind. Again, I mean, there were certainly, you know, allegations of corruption and all of that was sort of after the time I spent with her. But we could see that there was a kind of megalomania, I think.
13:54 Alec Baldwin? Right.
13:54 Speaker 06 That she was prey to.
13:56 Alec Baldwin? Well, I think that's also very, you know, the potential for that is high because of the stakes and the whole flavor of the whole thing. You know, your husband's in prison for the rest of his life, presumably. He's a political prisoner. You're there and that. I mean, my ex-wife made a film there. We went to South Africa after they had bombed Planet Hollywood in Cape Town and the US Embassy in Nairobi. So the film was supposed to be in Kenya and it was moved to South Africa. And she went there and it was like roadblock, highway robberies. My ex-wife had to have a driver, a lead car armed, the driver with her armed, a bodyguard armed. They were pulling people over and raping and robbing people right before we got there. So, South Africa was not Disneyland, you know?
14:40 Speaker 06 No, it was not. But imagine being there during the state of emergency, you know, before Mandela was released from prison. It was just, I mean, absolutely extraordinary experience.
14:50 Alec Baldwin? You go from life and you're there for a while. You didn't pop in and out of these places quickly. You were there at life for.
14:56 Speaker 06 Eight years.
14:56 Alec Baldwin? For eight years.
14:57 Speaker 06 Yeah.
14:58 Alec Baldwin? And when you leave life, you go to ABC?
15:01 Speaker 06 Actually CBS first.
15:02 Alec Baldwin? So you did, you were at 60 Minutes?
15:03 Speaker 06 Yeah.
15:04 Alec Baldwin? So that was before ABC?
15:05 Speaker 06 Yeah.
15:05 Alec Baldwin? So you were at 60 Minutes for how many years?
15:07 Speaker 06 What happened was I met Diane Sawyer, who was in her second year at 60 Minutes. And in need of a associate producer. And I went to work for 60 Minutes.
15:21 Alec Baldwin? And you were there from 86 to 91?
15:23 Speaker 06 That's right.
15:24 Alec Baldwin? 91, you go to ABC. Now, what was your experience like at 60 Minutes? We're going to get into just a little bit about wither CBS News.
15:30 Speaker 06 It was just phenomenal. I mean, it was really an exciting period of my life. And the very first thing I did was I said to Diane Sawyer, you know what? Give me a plane ticket to Honolulu and let me see if I can get Emelda Marcos. Emelda Marcos and her husband Ferdinand, the dictator of the Philippines, had fled, had just fled the Philippines. They were in Honolulu. They were holed up in a bunker there. The entire world press corps was trying to get to them. And I liked my chances of getting them. So I jumped on a plane, flew out there, called Diane from the compound, said, how soon can you get here because I've got Emelda Marcos ready to go? And she couldn't make it.
16:14 Speaker 06 And so the next thing I knew on my first day at 60 Minutes, two camera crews were flying in and I was interviewing Emelda Marcos and Ferdinand for 60 Minutes. Which I did. We sent the transcripts back, sent the tapes back to New York. They were transcribed. Don Uwitt, the legendary executive producer, read the transcripts before I flew back. And I walked in the door and Uwitt is standing there with Mike Wallace, the famous star of 60 Minutes. And he looks at me, he goes, way to go, kid. And I'm feeling pretty heady at this point. And I go, well, you know, Don, there's a moment, you may not be able to see it in the transcript, but there's a moment where Emelda doesn't quite lose it, but she gets all misty eyed.
16:59 Speaker 06 And Uwitt looks at Wallace and looks at me and says, kid, if you were any good, she would have cried. That was my introduction to network television.
17:07 Alec Baldwin? Now, let me ask you this. In the 60 Minutes period, you interviewed John Connally. I'm assuming that's the governor of Texas.
17:14 Speaker 06 That's right. So Connally was really fascinating, kind of larger than life character. He had been Treasury Secretary under Richard Nixon. He was at one point considered a real possibility as president. He ran, he tried to become president. He won one delegate, spent a fortune. But we went and saw him right after he had this real fall from grace. I mean, he declared bankruptcy. He lost everything he had. This was in the mid 80s. Eighty seven, I guess, around the recession of that time. But the real estate market collapsed and took all of Connolly's possessions with him. And he's sitting in a ranch house with all the furniture removed and, and talking about
17:56 Speaker 06 that fall from grace, but also talking about being in the limousine with JFK.
18:02 Alec Baldwin? Oh, God.
18:03 Speaker 06 And he and Nellie told us that story, you know, moment by moment. That was just absolutely riveting. Connolly barely survived it and obviously JFK did not.
18:14 Alec Baldwin? What did he say about that that you can recall? Anything? Because I mean, I'm a conspiracy nut. Like, I'm not gonna lie.
18:20 Speaker 06 Yeah, he was not a believer in a conspiracy. He believed that that bullet really was magical, you know, that that bullet.
18:27 Alec Baldwin? Zigzagged everywhere.
18:28 Speaker 06 Zigzagged and came out of his wrist or wherever it was. I forget now. But the other fascinating thing was climbing into his pickup truck. I'll never forget it. And John Connolly's driving and Diane Sawyer's in the passenger seat and I'm in the back with a, with a cameraman. And we drive to his old homestead where Connolly and Diane Sawyer start talking about Richard Nixon.
18:50 Alec Baldwin? Who Diane had worked for.
18:51 Speaker 06 Who Diane had worked for. Those two maybe knew Nixon better than anyone you could think of. So it was, it was amazing. And of course, he pointed out the homestead where he's, he said, I used to walk barefoot behind a mule over here. And he said, and one day I saw a fancy car go by. And I said, someday I'm gonna be driving that car. So it was some, um, pretty amazing experiences.
19:16 Alec Baldwin? Diane Sawyer, who of course enjoyed a great career, then she left for ABC as well, correct? Did you connect with her again at ABC?
19:23 Speaker 06 I did.
19:23 Alec Baldwin? You did?
19:23 Speaker 06 I did, yeah.
19:24 Alec Baldwin? So she was happy to see you when you showed up at ABC?
19:26 Speaker 06 I don't know about that.
19:27 Alec Baldwin? Right, okay.
19:28 Speaker 06 I was happy to be welcomed there.
19:29 Alec Baldwin? Yeah, she was great on that show. People forget how wonderful she was in that. She was a really good television journalist.
19:35 Speaker 06 Well, she, she and Sam Donaldson launched a show called Primetime Live. Primetime Live, as Sam would say. And Roone Arledge, at that point, was hell-bent on trying to compete with 60 Minutes. And lured her over and brought Sam Donaldson out of the White House and put them together as a team. And for a while, we had the resources to do a lot of pretty serious investigative hidden-camera stuff, which we did for a number of years. It didn't last forever. But, you know, at one point, I literally set up a phony medical clinic in downtown Los Angeles and hung up a shingle and rigged the place with hidden cameras. And we advertised ourselves
20:20 Speaker 06 as a general practitioner doctor's office. And we watched and rolled tape as crooked doctors and brokers beat a path to our door, offering us illegal kickbacks for our patient referrals.
20:33 Alec Baldwin? For tests and so forth.
20:35 Speaker 06 Yeah. And after four or five months of running this phony clinic, you know, we invited them all back and Diane confronted them. And anyway, we won an Emmy for that. But it was, those were the days when networks really had, were throwing money at pretty serious investigative journalists.
20:56 Alec Baldwin? Exactly.
21:01 Alec Baldwin? Journalist and author Chris Whipple, if you enjoy conversations about the inner workings of important magazines, check out my episode with former Vanity Fair editor Tina Brown.
21:13 Speaker 07 Well, I think I'm a compulsive reporter, actually. I mean, I have what I think of as observation greed, right? Most of the time, I'm propelled to go out, not because I actually want to go out, but I think, I gotta see that. I, you know, I need to see that.
21:28 Alec Baldwin? Curious.
21:28 Speaker 07 Curious. I'm really curious. And I have a great desire to report on the action.
21:36 Alec Baldwin? To hear more of my conversation with Tina Brown, go to here'sthething.org. After the break, Chris Whipple details one piece of advice former White House Chief of Staff Reince Priebus gave to Susie Wiles.
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23:15 Speaker 03 Hey, it's Nile Rodgers, host of Before the Moment, a Lincoln original series. I'm driving across the country, meeting some of today's most fascinating artists. We're exploring the stories before the moment that changed everything. This week, I'm joined by rising star Sienna Spiro. What is so fascinating to you about impermanence?
23:37 Speaker 02 Everything about us, everything we do, is temporary. And I just got terrified of that. You know, what we do with our time and how I feel like the way the world is today and how fast-paced it is and how much we don't even acknowledge anything around us. How I felt temporary to the people around me and how that made me scared and how much I wanted to last and make an impact on people. And I guess to change the way I looked at things and to change myself and to change how I guess I approached everything.
24:03 Speaker 03 In my life, it's important that things are impermanent because nothing would feel special and enjoying, you know, learning to love with knowing it's not going to last. Experience before the moment, a Lincoln original series on the iHeart Radio app, YouTube, or wherever you get your podcasts.
24:22 Alec Baldwin? I'm Alec Baldwin, and this is Here's the Thing. In 1978, Chris Whipple began his reporting career at Life magazine, where he covered countless historic events and interviewed many significant figures such as Winnie Mandela, Desmond Tutu, and Ted Kennedy. Whipple secured an interview with Ted Kennedy during the 1980 presidential election, but his interview did not quite go as planned.
24:50 Speaker 06 Absolutely amazing story. A story that didn't appear in Life because, for reasons you'll understand in a second. But what happened was, I was at the Kennedy compound in Hyannis Port the day Roger Mudd did that infamous interview.
25:06 Alec Baldwin? Why do you want to be president?
25:07 Speaker 06 Why do you want to be president? And it was produced by Howard Stringer and Andy Lack, two guys you'd never heard of. And they were chasing me around the lawn trying to, because they thought this was their exclusive. And so all of a sudden, this kid from Life magazine is there with a photographer, and we stood our ground. Anyway, we watched this thing happen. And Roger Mudd asks the famous question, and Kennedy is utterly inarticulate, cannot complete this, can barely complete the sentence, couldn't answer the question, why do you want to be president? Afterwards, Mudd takes off his microphone and walks down to the seawall, and I walked down behind him. And I congratulated him. I said, Roger, hi, I'm Chris Whipple. That was amazing. He goes, really?
25:52 Speaker 06 You think I got anything? He had no idea what he had. It was pretty clear to everybody else who was watching it, or I mean, we didn't know it would end his campaign, which essentially it did. But Mudd didn't realize what he had. That was the modesty of the, of the man. I thereupon had my.
26:11 Speaker 06 Ten minutes or fifteen minutes with Kennedy riding in the limousine from the compound down to the dock where Patrick, his son, was waiting on the sailboat to go for a sail. And Kennedy had all, he was catatonic. He had this like thousand yard stare and I would ask him questions and get no response. And to this day, I don't know what was going on. Whatever happened, boy, he didn't have it that day. And I think it ended his campaign.
26:40 Alec Baldwin? So tell me about CBS and what you think has happened there. Does you think that this is going to wind up happening everywhere?
26:46 Speaker 06 Wow, it's painful to watch. I mean, for, for those of us who were there during the glory days. I'm not always the hair on fire guy when it comes to what's going on at CBS right now because I can remember, let's take for example, what happened recently with Barry Weiss spiking or at least delaying that story about the, that terrible prison in El Salvador. CCOT. I'm old enough to remember, even though it was after I left 60 Minutes, when Don Newt, the executive producer spiked the story about Big Tobacco. And it was later turned into a movie, as you know.
27:24 Alec Baldwin? The Insider.
27:25 Speaker 06 The Insider with Al Pacino. And that story eventually ran and it ran to devastating effect. I mean, really changed everything. Lowell Bergman was the producer, but I knew Lowell when he was there. So I don't think it's the end of the story and I think, I think that CCOT story will run. I mean, a lot of people seen it because there was a bootleg version of it that the Canadians put out. A lot of people saw it. But boy, they're going through a rough period.
27:51 Alec Baldwin? But I wonder if the other networks as well, that, that news, which was an edict from the FCC if I recall, these are public airwaves and you have to have some news programming. They ordered that.
28:02 Speaker 06 Yeah.
28:03 Alec Baldwin? And eventually tried to turn it, you know, away from a lost leader, if you will, or whatever comparison you want to make.
28:08 Speaker 06 Yeah.
28:09 Alec Baldwin? And they, you know, the news is big business, but I wonder if it's not big business anymore and they all want to get rid of it in some way or just cut the cost to nothing.
28:15 Speaker 06 Yeah, I think you may be right. And nobody under 75 is watching the, the network news broadcast. I spoke to a 12th grade class, really bright kids in Greenwich, Connecticut, affluent kids. And they're getting their news from TikTok and dinner with their parents.
28:35 Speaker 06 It's not a pretty picture.
28:38 Alec Baldwin? I met a party once at John Eastman's house, McCartney's brother-in-law, Lynda Eastman's brother, and I'm there and it's, John Eastman and his wife would have these fabulous parties in the summertime at their house, and all these people there that you admired. And I'm sitting down with Holbrook, who was the loveliest guy on earth and the most charming man on earth, and Holbrook sits there and says to me, "Read the forty pages in Halberstam, and that'll tell you everything about me. Don't even bother with anything else. That's McNamara."
29:05 Speaker 06 Yeah.
29:06 Alec Baldwin? And he goes, "And I want you to read it and then call me and we'll have dinner." He was very kind to me. He said, "Let's have dinner or lunch," and then he died two weeks later or something like that, right on the heels of that.
29:14 Speaker 06 Wow.
29:15 Alec Baldwin? What was your relationship with him like?
29:16 Speaker 06 Holbrook was an unbelievable character. I mean, I was a kid at a college, you know, with hair down to my shoulders and completely out of my depth as his assistant at foreign policy, but I must have done something right because he just became a mentor and a great friend, and the reason I wound up at Sixty Minutes, one day, I was back from an assignment for Life, was walking through the lobby of the Jefferson Hotel in Washington, and Holbrook comes out of the dining room, and we bump into each other, and he goes, "Congratulations. Listen, I just read your piece on Marcos. You got the quote of the year from Marcos." Of course, he'd read Life magazine. He read everything. And he goes, "Listen, you gotta have lunch with me and Diane."
30:00 Speaker 06 Well, Diane was his then-girlfriend, Diane Sawyer, and that was how I met Diane and wound up eventually at Sixty Minutes.
30:09 Alec Baldwin? So, let's talk about, what's your relationship with Vanity Fair? The piece goes because you had an ongoing relationship with them, and you'd written for them before?
30:17 Speaker 06 I have.
30:18 Alec Baldwin? When you first started writing, who was in charge? Graydon?
30:20 Speaker 06 So, Graydon Carter was in charge when I began writing for Vanity Fair. I did a number of pieces, including the first interview with Reince Priebus after he was...
30:31 Alec Baldwin? Shown the door.
30:33 Speaker 06 On the tarmac. He was literally on a rain-soaked tarmac under Air Force One when Trump tweeted that his services were no longer needed. That was the way Trump rolled during the first term with White House chiefs. But anyway, I got to know Reince. Interviewed him, the very first thing he said to me, I'll never forget, I met him at a bar in Georgetown, and he came over to me and he said, "Take everything you've heard and multiply it by fifty."
31:05 Speaker 06 And we were off to the races and I did a piece for Vanity Fair after that. The irony here is that fast forward now, eight years, there was a gathering for Susie Wiles before she became White House Chief of Staff. Jeff Snipes, the outgoing White House Chief for Joe Biden, invited a bunch of chiefs to come and give Wiles some advice. They went around the table and they got to Reince Priebus and Priebus looked at Wiles and said, "One thing, don't talk to Whipple."
31:36 Alec Baldwin? Interesting.
31:37 Speaker 06 She evidently didn't take it to heart. Every once in a while in a reporter's career, lightning strikes and this was one of those cases. White House Chiefs of Staff never talk to reporters on the record or very rarely.
31:51 Alec Baldwin? Not for that length of time either.
31:53 Speaker 06 You know, I wrote a book on the Biden White House, on the first two years of the Biden White House, got to know Ron Klain pretty well, interviewed him multiple times, always on so-called deep background with quotation approval required before you publish. None of that with Susie Wiles.
32:09 Alec Baldwin? So they came to you, you pitched them? What did the Wiles thing come up with? Who originated that idea?
32:14 Speaker 06 So I did. What happened was, I was writing and I still am writing a book on a history of presidential campaign managers from 1968 to the present. It's a rogues' gallery of great characters from, you know, John Mitchell to Lee Atwater to James Carville to Susie Wiles, who ran Trump's campaign. So I called up Wiles. She was driving 10 days before she became White House Chief. She's driving from Mar-a-Lago to her place in Punta Vedra, about four hours north in Florida. And we start talking and I can't believe it.
32:51 Speaker 06 She is open and unguarded and on the record and smart and funny and charming. And I got off the phone and I said to my wife, "You're not going to believe this." And she didn't, but it was true. She was on the record during that first conversation, except when we mutually agreed to go off very briefly. And for the next 11 months, we just kept talking. Now, I should say that what happened was initially, she knew I was writing a book about presidential campaign managers. That's why she was talking to me. I quickly realized that what she really wanted to talk about was Trump 2.0.
33:34 Speaker 06 And she, he told me, I just got off, just got off the phone with Hakeem Jeffries, and I told him, you're going to see a whole new Trump. Trust me. Anyway, so a couple of interviews into this process, I said to her, well, listen, Susie, Vanity Fair wants to do a big piece on Trump 2.0. And she said, great, congratulations. She was all in.
33:59 Alec Baldwin? Wow, that's amazing to me. Looking back at your books, because you mentioned the Biden book, this is not a serious question, obviously, but I just, I can't help it. Should we have an age limit for the President of the United States? I mean, we got two guys that are rounding the corner at 80, and both of them have serious issues, maybe neurologically, who knows, or whatever. And I wonder, should we, should we go that, well, you can't be President until you pass a certain physical?
34:22 Speaker 06 Maybe there should be, yeah, maybe there should be. Look, I think that it was Joe Biden's 11th hour abdication from the race, which left Kamala Harris with too short a runway.
34:34 Alec Baldwin? Exactly, that's what I said, I used that phrase, too short a runway.
34:36 Speaker 06 To mount a serious race against Trump. Was a scandal and a tragedy, a tragedy for Biden, obviously, but also for the Democratic Party and arguably the country. There's no question about it. Now, I don't agree with Jake Tapper that Biden was Woodrow Wilson, non compos mentis over in the corner while everybody else was governing by autopen. I think that was nonsense. I think Biden was actually making decisions behind closed doors. What he couldn't do was campaign. He couldn't do anything, as we all saw in that infamous debate.
35:15 Alec Baldwin? I wonder if we're, we're married now to this kind of hawkish or semi hawkish presidential figure, where they didn't have to talk tough. You never hear anybody talk about peace anymore, never. Nobody talks about peace in the Middle East or in Ukraine, it's all war.
35:30 Speaker 06 Yeah, no, you really wonder. I was joking with somebody earlier today that Rahm Emanuel, if he wants to make a run, doesn't even have to clean up his language after Trump.
35:41 Alec Baldwin? Can you believe this?
35:42 Speaker 06 The F-bomb, you know, every other sentence. But, no, I mean, seriously, you really do have to wonder whether we've turned some kind of corner where politics will be coarse and nasty, brutish and short.
35:56 Alec Baldwin? You've profiled, in terms of the chiefs of staff and so forth, but beyond that, you've been around these people forever. The one thing that I was the most surprised by in the first term, and especially now in the second term, I didn't know there were that many people who were like-minded with Trump. I didn't know there were that many people to staff a White House and their other offices to come to. And I'm appalled by how many, I don't want to say evil, but hard-line vicious, non-empathetic people are in Washington. Hundreds of them showed up there to work. Did that surprise you, or did you know they were always there, waiting for their moments?
36:32 Speaker 06 It surprised me, too. You know, the difference between Trump 1.0 and 2.0, there are a number of differences, and one of them is Susie Wiles. She runs a tighter ship. But a major difference is that everybody's reading from exactly the same playbook. With certain, you know, minor exceptions, I mean, Susie, in the Vanity Fair piece, Susie Wiles told me there was real disagreement, a real battle over tariffs. But, you know, other than that, they're essentially all reading from the same playbook. And you don't have, obviously, as everybody's pointed out, you don't have a Jim Mattis, and you don't have a Rex Tillerson, you don't have people who were trying to...
37:12 Alec Baldwin? Who had opinions of their own.
37:13 Speaker 06 Yeah. And that's one of the reasons why there's been a lot of speculation about why Susie talked to me, why Susie Wiles would do this. And, again, I think it's pretty simple at the end of the day, which is that they're in this bubble, and they forget that a lot of the crazy stuff that they're saying to each other all day long sounds insane on planet Earth. But they're not on planet Earth. They're in this bubble, exponentially more so in the Trump White House than in any other White House. And I think that when the Vanity Fair piece landed, they were surprised.
37:55 Alec Baldwin? Journalist, author, and documentary filmmaker Chris Whipple. If you're enjoying this conversation, tell a friend and be sure to follow Here's the Thing on the iHeart Radio app, Spotify, or wherever you get your podcasts. When we come back, Chris Whipple talks about why Bill Clinton might have been a one-term president, were it not for his chief of staff, Leon Panetta.
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39:54 Speaker 03 I'm driving across the country, meeting some of today's most fascinating artists. We're exploring the stories before the moment that changed everything. This week, I'm joined by Miguel. That last year, finishing that record was the hardest experience of my life. To find your creativity and to believe in yourself, because... Somewhere in the midst of it,
40:18 Speaker 03 I stopped believing that my voice mattered and that I could find it again. That's a challenge. I was not feeling very confident creatively, only,
40:30 Speaker 03 again, defiant in my belief that
40:36 Speaker 03 what this is about is express something honest, say something honest. Experience before the moment. A Lincoln original series on the iHeart Radio app, YouTube, or wherever you get your podcasts.
40:55 Alec Baldwin? I'm Alec Baldwin, and this is Here's the Thing. In 2013, Chris Whipple wrote and produced the documentary series titled The President's Gatekeepers for Discovery Channel. The series spanned nine presidential administrations and featured interviews with all nine chiefs of staff. After the series, Whipple continued his research. His book, The Gatekeepers: How the White House Chiefs of Staff Define Every Presidency, was a New York Times bestseller. The book was the first of its kind, giving a behind-the-scenes look into White House chiefs of staff. Most recently, Whipple profiled the current White House chief of staff, Susie Wiles, for Vanity Fair in 2025.
41:41 Alec Baldwin? Out of all the chiefs of staff Whipple had interviewed and researched over the years, I was curious which he admired the most.
41:49 Speaker 06 James A. Baker III for Ronald Reagan and Leon Panetta for Bill Clinton. I think you can make a really strong case that there would have been no Reagan revolution without Jim Baker. And I'll give you an example. Ronald Reagan, when he came into office, was hell-bent on tackling Social Security, cutting. Jim Baker sat him down and explained, "Look, Social Security is the third rail of American politics. You touch it, you get electrocuted. You need, let's, let's put that off." And the result was that Reagan pivoted to tax cuts and was re-elected in one of the largest landslides in history. Eighty-four.
42:32 Speaker 06 Yeah. Now, Baker did it with help from Nancy Reagan, but he was smart enough to round up the allies he knew he needed to do that. Bill Clinton might have been a one-term president if not for Leon Panetta. Why? Eighteen months into Clinton's presidency, he was dead in the water, paralyzed with all kinds of many scandals. Gingrich. Scandals. Gingrich, Travelgate, Whitewater, you know, crazy little scandals that we've almost forgotten by now. But he was in deep trouble, and the White House was really ineffective. And Leon Panetta came in and just turned it around. He imposed real discipline on a guy who was pretty hard to discipline. But Panetta did it. Panetta was the kind of guy
43:17 Speaker 06 who could, who could walk into the Oval Office, close the door, and tell Bill Clinton what he didn't want to hear. There's nobody who can do that with Donald Trump. Of course not. Even though Susie Wiles, here's the thing about Susie Wiles. We'll never know what might have been, in a sense, because Susie Wiles has a kind of magic with Trump. He trusts her. He pays attention to her when she speaks. And yet, it's clear, and I document this over the course of 11 months of talking to her, it's just clear that she has chosen not to tell him hard truths. You know, she said, "I've had White House chiefs tell me,
44:00 Speaker 06 some of my predecessors say they have these seminal moments when they have to confront the president about a constitutional issue. I don't have that." Well, an empowered White House chief, an effective White House chief... Has to have that. You have to be able to tell the president what he doesn't want to hear.
44:18 Alec Baldwin? I wonder sometimes, you know, who goes into that job and when you get the presidents here, there's a lot, there's a volume of people who could take that job and who want that job. But is that part of it where they realize they can depend on you to tell them the truth? Who was Obama's chief of staff?
44:33 Speaker 06 Yeah, absolutely. So Obama had four.
44:35 Alec Baldwin? Right.
44:36 Speaker 06 Rahm Emanuel was his first.
44:37 Alec Baldwin? Right.
44:37 Speaker 06 Dennis McDonough was his last.
44:39 Alec Baldwin? Right.
44:39 Speaker 06 Bill Daley was his second and Jack Lew was his third. And, and not easy. I mean, it's, it's, it's.
44:46 Alec Baldwin? Did they have his ear?
44:47 Speaker 06 Believably difficult job. I think Rahm got through to him. Bill Daley, not so much.
44:53 Alec Baldwin? Right.
44:53 Speaker 06 Uh, they just didn't click. And I think Lew more so and Dennis McDonough was the most successful.
45:00 Alec Baldwin? Really?
45:00 Speaker 06 Yeah.
45:01 Alec Baldwin? Because Obama seems so inscrutable.
45:03 Speaker 06 Yeah.
45:04 Alec Baldwin? He doesn't seem like you have to really drill down.
45:06 Speaker 06 Yeah.
45:07 Alec Baldwin? To get down to the real Obama.
45:08 Speaker 06 Exactly.
45:09 Alec Baldwin? He wasn't going to share anything. He only shared on an as-needed basis with people.
45:13 Speaker 06 Exactly.
45:14 Alec Baldwin? Whereas Clinton always seemed to be more avuncular than that. Now, the spymasters, how the CIA director shaped history and the future. What do you think about the intelligence apparatus we have in place now?
45:25 Speaker 06 Well, it's a really good question because on the one hand, the thing that, very much like a White House chief of staff, a CIA director has to be able to tell the president hard truths. And it's not at all clear to me that John Ratcliffe is the guy to do that. I mean, Ratcliffe is, you know, famously partisan and the danger of that is that, you know, the CIA director is the guy we count on to prevent another 9/11 or worldwide pandemic, all kinds of terrible things. And if you can't count on that guy to tell you hard truths, you're in trouble. Having said that, look, I mean, clearly we've had a couple of operations that have done, been very successful in the short term.
46:10 Speaker 06 I mean, the bunker busting operation in, in Iran, the snatching of Maduro, whatever you may think of that idea, was pretty effectively executed. So the CIA is doing something right, but we're just going to have to see all, how all of this plays out because these are. Are a long way from over.
46:29 Alec Baldwin? I've always maintained when I was more involved in politics and candidacies per se, I always used to say that the former director of the CIA or the Energy Department were automatically disqualified from being president because they woke up every morning, had to lie to the American people for a living. When I said that to Bill Clinton, he goes to me like, you can leave now, you know what I mean? But he was about to run for something out of coming out of New Mexico.
46:52 Speaker 06 Yeah.
46:52 Alec Baldwin? What are you working on now?
46:54 Speaker 06 Actually, I've gone back to the book that I was working on when I first started talking to Susie Wiles for Vanity Fair, for the piece that became a Vanity Fair piece. And that is the history of presidential campaign managers. The working title is The Kingmakers, and it's a really fascinating cast of characters.
47:12 Alec Baldwin? Yeah, right.
47:12 Speaker 06 Sixty-eight, an unbelievable campaign. You know, two assassinations, at least two, more than that. MLK, Bobby Kennedy, Hubert Humphrey, almost caught Nixon in a photo finish because, interestingly, he really broke with LBJ on the conduct of the Vietnam War. I always thought Kamala Harris should have taken a page from Hubert Humphrey and distanced herself from Biden, but that's another story, 2024.
47:42 Alec Baldwin? Mitchell was his campaign manager?
47:44 Speaker 06 John Mitchell, campaign manager in sixty-eight. H.R. Haldeman was sort of his deputy.
47:49 Alec Baldwin? There's such a flurry of facts in All the President's Men. I participated in a staged reading of the screenplay of All the President's Men.
47:56 Speaker 06 Is that right?
47:56 Alec Baldwin? And Carl and Bob Kane.
47:59 Speaker 06 My favorite story about, tell me if this is true. My favorite story is that the screenplay was a mess. The late William Goldman, who was a terrific screenwriter.
48:10 Alec Baldwin? Great.
48:10 Speaker 06 But the screenplay was a mess. Carl Bernstein took it home one night and Nora Ephron rewrote it overnight.
48:17 Alec Baldwin? Well, that may be so. Can't rule that out. He was married to her for that period of time. It's amazing, the facts that come flying, but I forgot that Mitchell was his campaign manager.
48:26 Speaker 06 Yeah.
48:26 Alec Baldwin? In that sixty-eight campaign.
48:27 Speaker 06 Oh, absolutely. And then became his Attorney General and ended up in prison, along with a bunch of others.
48:33 Alec Baldwin? Jesus Christ. Oh, those were the days.
48:35 Speaker 06 Yeah.
48:35 Alec Baldwin? When they ended up in prison.
48:37 Speaker 06 So anyway, sixty eight is the beginning and I, when I'm done, I'm gonna bring it all the way up to the present, but it's been amazing. Gary Hart, I was talking to Gary Hart, who, who lives on a, a road called Troublesome Gulch in Colorado.
48:49 Alec Baldwin? I saw the big article in the Times about him years ago.
48:51 Speaker 06 Gary Hart famously, his campaign fell apart after a scandal with a girl named Donna Rice.
48:57 Alec Baldwin? Of course.
48:58 Speaker 06 Uh, and, uh, but boy, does Hart have some stories.
49:01 Alec Baldwin? Monkey Business was the name of the boat.
49:02 Speaker 06 The name of the boat. But boy, does Gary Hart still have some stories to tell.
49:07 Alec Baldwin? I want to say thank you. What an amazing career you've had. What a great career you've had. To, to do journalism and do television news and then do these books. It's just amazing.
49:17 Speaker 06 Thanks.
49:18 Alec Baldwin? I hope you're happy with your career. You've had an amazing career.
49:21 Speaker 06 Well, thanks for having me.
49:24 Alec Baldwin? My thanks to journalist and author Chris Whipple. This episode was recorded at CDM Studios in New York City. We're produced by Kathleen Musso, Zach McNeese, and Victoria DeMartin. Our engineer is Isaac Kaplan-Wulner. Our social media manager is Danielle Gingrich. I'm Alec Baldwin. Here's the thing is brought to you by iHeart Radio.
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